


Heather

by Ashcat252



Category: Supernatural
Genre: Angst with a Happy Ending, Bottom Sam Winchester, Drag Queens, F/M, Feminine Sam Winchester, Gay Sam Winchester, M/M, Minor Character Death, Mutual Pining, Phone Sex, Pining Sam Winchester, Psychic Bond, Top Dean Winchester/Bottom Sam Winchester, Underage Sex
Language: English
Status: In-Progress
Published: 2020-08-26
Updated: 2020-11-10
Packaged: 2021-03-06 22:27:30
Rating: Explicit
Warnings: Underage
Chapters: 3
Words: 11,904
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26116441
Author URL: https://archiveofourown.org/users/Ashcat252/pseuds/Ashcat252
Summary: Sam and Dean separate. And for years, Sam tried to be okay with that. Even if that meant faking a smile during the day and sleeping with his big brother’s sweater at night.And when Dean finally visits with his girlfriend, Sam swears his jealousy isn’t why he’s suspicious of her, this Heather. And he won’t rest until he figures out why.
Relationships: Dean Winchester/Original Female Character, Dean Winchester/Sam Winchester, Sam Winchester/Original Male Character(s)
Comments: 10
Kudos: 37





	1. Chapter One

_**2001** _

Sam Winchester held onto his brother’s sweater for dear life, like he did that one lonely Christmas morning years ago, and every night after that. The difference was he was beaten and bloody that time around. He hadn’t even been on a hunt since he was thirteen, so naturally Sam was out of his element and _scared_.

He shut his eyes tight and tried to quiet his breathing so his captor wouldn’t hear him. He tried his best not to remember the too recent memories of what got him there in the first place and pretended not to hear the sound of foot steps getting closer and closer.

~*~

_**December 3rd, 1996** _

He couldn’t remember exactly what caused him to get so angry. Sam was just thirteen and already so tired of everything their father was putting them through. He was sadly used to moving from place to place, but one thing was for certain: Sam hated the cold.

The cabin they were staying in was old and had no electricity. All they had to keep warm was the fire in the living room, which Dean always kept going until nightfall. Sam still felt cramped. He wanted to be in school but John said they wouldn’t be staying long enough to get enrolled which felt like utter bullshit.

It just meant Sam was forced to sit alone as Dean went into town to find any type of work he could, while John stayed gone to finish up his latest hunt. And maybe find a lead on his main mission to kill the demon that took Mary away from them. Sam wasn’t sure anymore.

Sam was slowly loosing his mind and it only got worse once Dean got home and took off his thick sweater and threw it against the couch. The tip of his nose and freckled cheeks were flushed red from the cold.

He was as beautiful as ever.

Sam wrapped his arms around himself and dug his nails into his arms until he could feel it through the fabric of his thermal. Thinking of his brother that way was a recent development and it only served to piss him off more.

“You’d be warmer if you kept the fire going properly.” Dean grumbled as he threw a log into the hearth. “You’re old enough to start doing this yourself, Sammy.” He sighed as he walked into the tiny kitchen to start cooking that nights supper.

His words ate away at Sam until the boy couldn’t hold his tongue any longer, “This is stupid, Dean. This cabin, Dad’s hunt. It’s just— _stupid_! I should be in school right now!”

Dean leaned against the stove, his back to his brother as Sam went on and on about how much he hated his life. Not once had he thought about what day Dean could have had. Not once did Sam think to ask. He was too consumed with his own problems to even consider it.

“And then there’s you. You always do exactly what dad tells you, even when he’s clearly wrong. Do you even think for yourself-”

“ _Sam_.” Dean ground out, his tone a clear warning for his brother not to continue. But Sam wasn’t in the mood to hear it. He had to let it out, no matter the cost.

“Do you really want to be a mindless solider for the rest of your life? Hunting for demon that’s long gone? What’s the point? It’s not like it’s gonna bring mom back-”

Sam knew what he was doing by bringing up their mom. He wasn’t stupid. He wanted Dean to be just as mad as he was. What he didn’t expect, however, was for Dean to turn around and smack him across the face.

They both stood there in pure shock as the smack echoed through the cabin. Dean had never hit Sam like that before. Of course they’d sparred for practice with each other, and even had the occasional fight, but it had never been like that.

“Sammy...” Dean tried, but Sam didn’t want to hear it. His cheek burned and tears flooded his eyes. He refused to cry in front of Dean. Instead, Sam turned and ran, grabbing Dean’s sweater because his weren’t nearby.

December in the Colorado woods were unforgiving. He had no shoes on; just the socks on his feet, his pajamas and Dean’s sweater. He couldn’t find it in him to care about the cold as sobs wracked through his chest. He needed to get away from it all, especially from the sound of Dean calling out for him.

Sam ran through the thicket, not once caring if he got lost. Maybe that was what he wanted. To get lost and just disappear. One last thing for his father and Dean to worry about.

And maybe if his vision wasn’t clouded with a flood of tears, he would have noticed the root just barely sticking out the snow. Instead it caused him to lose his footing, and made him tumble down the upcoming hill.

“Sammy!” Was the last thing the boy was able to hear before his body slammed into a too close row of trees, knocking him out cold.

When his eyes fluttered open, he was almost certain it was a dream as he looked up at the cabin’s ceiling. That was until his big brother got into view with a steaming pot of stew.

“Can you eat?” Dean asked, his tone soft. The question woke Sam up fully and made him fully recognize the pain. He sat up too fast and groaned into his palm.

“Be careful.” Dean said as he sat the bowl down onto the coffee table. He let his hand fall to Sam’s shoulder and from there the younger Winchester could see the blood staining his big brother’s sweater.

“Y-your sweater...” Sam stammered. Dean just shook his head, his smile soft.

“It’s just polyester, Sammy.” He joked as he rubbed his thumb across the almost dry specks of blood. “You can keep it. It looks better on you anyhow, though it’s a little big.”

Sam watched the steam leave the bowl and tried not to think about the way Dean’s hands felt against his scalp. He tried his best to ignore the blush creeping onto his cheeks.

“I’m sorry for hitting you.” Dean said as his fingers brushed against his little brother’s cheek. “I had a long day and hearing you say all that stuff... it just sent me over the edge. Seeing you on the ground like that though, that was scary.”

Sam had never heard dean talk so softly before. It made him feel warm. All Sam could think to do was throw his arms around his big brother, tears filling his eyes once again.

“No, De, _I’m_ sorry. Should have never talked to you like that. All you’ve ever done is take care of me and y-you... you just deserve so much more.” By the end of it, Sam was practically sobbing. Dean let out a breathy laugh and returned the embrace. He let his little brother cry it out until his breathing finally calmed.

Dean pulled back slightly and Sam looked up at him, knowing full well he must have looked so silly with his puffy eyes and red cheeks.

“There’s nothing I’m ever gonna want more than to take care of you.” He said, his hands still on Sam’s cheeks. His smile was warm and green eyes were all too soft. All Sam wanted to do in that moment was kiss him and the thought alone terrified him.

Before Sam could do anything he’d most likely regret, Dean finally pulled away. His laugh was strained and awkward as he looked away from his little brother.

“Anyway. Enough of this chick-flick moment. Let’s eat.” Dean got up from the couch and to the kitchen, leaving Sam alone with his thoughts and a cooling bowl of stew.

~*~

_**December 25th, 1996** _

It didn’t take long before the Winchester family left that Colorado cabin and found themselves at Singer Auto Self Service Salvage Yard.

They were staying for awhile, so Sam was finally in school. It served as the perfect distraction from the ever growing thoughts about Dean. Didn’t stop them fully, however, but Sam was willing to take what he could get.

Sam woke up early that morning happier than he’d ever felt about Christmas in his entire life. He didn’t expect any presents but he did have one just for Dean, thanks to Bobby.

It wasn’t anything fancy, but it felt special. Bobby thought so too. Sam had it wrapped up the best he could under his bed. It was weird having his own room and not sharing a cramped motel bed or pull out couch with Dean. He missed it.

As soon as Sam opened his bedroom door, he was met with the smell of breakfast. Bobby always made sure to give them some type of normalcy while they were there with him and Sam couldn’t help but appreciate it. He slowly made his way down the stairs but stopped once he heard strained whispers coming from the kitchen.

“I thought you would have wanted this, Dean.” John said through a long sigh. Sam could practically envision his father rubbing a calloused hand over his tired features.

“I’m just not built for it, dad. Never have been.” Dean said, his tone barely above a whisper. Sam leaned in closer, careful as to not make the floorboards squeak beneath his feet.

“You and Sam deserve a normal life. Bobby is retiring and is offering you two a place to live and grow.” John said and Sam could feel his pulse quicken. A normal life was what he always wanted. He didn’t understand why it sounded like Dean was turning it down.

There was a long silence and Sam felt like he was going to burst. His grip was tight around the gift meant for Dean. Sam was in the middle of taking a step down so he could add his two cents but then Dean finally spoke and it made the boy’s stomach drop.

“Sam should stay. He’s not cut out for hunting like I am, dad, that much is clear. And I... I can’t stay. I’m a hunter. It’s what I am and what I always will be.”

Sam could hardly believe it. Dean wanted to abandon him. Hot tears filled his eyes as the present fell from his hands and tumbled down the stairs. Sam couldn’t find it in him to care.

“Shit, Sammy-“ Dean called out from the first floor like it just dawned on him that his little brother had been listening that entire time. Sam didn’t give a shit about anything but his bubbling anger as he slammed his bedroom door behind him.

He fell across the bed and buried his face in the pillow. He knew it was childish but it was either that or punch a wall, and he still had enough mind to know Bobby wouldn’t appreciate that.

He was just heartbroken that Dean would even suggest leaving him. He had a mix of feelings swirling inside of him and they were all so confusing and infuriating. It didn’t help that Dean made his way inside the room without knocking, ignoring Sam’s demand for him to leave. Instead, he sat on the edge of Sam’s bed and placed his hand on the back of his little brother’s head.

Sam hated how much he welcomed the touch. He should have been shoving him away. But more than anything, he wanted to feel Dean’s presence.

“Sammy,” Dean cooed. Sam grunted and just buried his face even deeper into the pillow. “Please, look at me and let me talk to you.”

Reluctantly, Sam did as he was told. He turned over onto his back, his face red and stained with tears. Dean’s features were oddly strained as he brushed Sam’s bangs from his eyes. He left his hand on Sam’s cheek and slowly used his thumb to brush away the wetness.

“De?” Sam’s voice cracked and it caused Dean to pull away and put his face in his hands. He watched as Dean ran his fingers through his own hair and tugged in visible frustration.

Sam sat up then and finally noticed the present he got for Dean sitting in his older brother’s lap. Though he was still angry, Sam felt as though he should at least try to lighten the mood.

“So... that’s for you.” Sam whispered. Dean eventually removed his hands and looked down at his lap. He gave a small smile and moved to unwrap it.

Once the paper was gone, Dean held the amulet in his hand and examined it. Sam bit his lip, suddenly nervous that Dean wouldn’t like it. Not that he should care. He should be livid. Dean was trying to leave him after all.

He couldn’t help but feel warm however once Dean put it around his neck. He watched as it fell against Dean’s shirt. It looked like it was always meant to be there.

“It suits me. You did good, Sammy.” Dean mumbled, but still made no move to look at Sam. The younger boy didn’t know what to do. His anger was boiling up inside him again, and he wasn’t sure if he could hold his tongue.

“Why are you so willing to leave me behind?” Sam asked carefully. He watched as Dean looked at him, his green eyes heavy with emotion, more than Sam had ever seen.

“It’s not like that.” Dean sighed, then added, “it’s just what’s best for you.” Sam couldn’t help but scoff at that.

“Best for _me_? What about you, Dean? Don’t you deserve a normal life too?” Sam asked, his tone just short of exasperated.

Dean shook his head, a humorless laugh escaping his lips, “It’s too late for me, Sammy.”

“That’s stupid.” Sam grumbled. It made Dean raise his brow. Sam couldn’t hold his tongue anymore.

“That’s a real stupid excuse to cover up the truth. Just admit you’re tired of always having to take care of me. Admit that you’d be better off without all this _extra baggage._ ” Sam’s voice broke near the end as more tears filled his eyes.

It was a truth he found hard to admit to himself. He always got in the way during hunts. Dean had to be right: Sam just wasn’t cut out for that life. They were better off without him.

“Sammy, no. That isn’t—you are _not_ baggage.” Dean said, his tone stern. When Sam just rolled his eyes, he leaned forward and placed his hands on his little brother’s cheeks, forcing the boy to look at him.

“I need you to understand that me leaving is taking care of you.” Dean’s tone was desperate but Sam was just as confused as ever.

“That makes no sense. I need you here, De.” Sam was just short of begging. He gripped at his brother’s wrists and let out a small sob, “ _please_.”

Dean shut his eyes and took in a deep breath. And when his eyes finally opened, he had an intense look in those pools of green that made Sam’s breath hitch. He didn’t know what to expect when his brother started to lean in, his instinct was to just let his eyes flutter shut.

Sam could practically feel Dean’s breath on his lips. His heart hammered in his chest as he awaited for the feel of the thing he’d dreamt about for weeks.

Dean’s lips ghosted against his own but instead pressed against Sam’s forehead. Sam still couldn’t help but gasp. He’d never felt Dean’s lips on his skin before and it only made him want more. They stayed like that for a few moments before Dean eventually pulled away, his forehead resting against Sam’s.

When Sam was able to open his eyes, he could see Dean’s tears, shame written on his face. Sam couldn’t help but let his thoughts race. Had Dean been feeling the same way? He could hardly believe it. Sam needed the answer, but before he could open his mouth to ask, Dean spoke.

“I have to find my own way, Sam. I can’t be the one to look after you anymore.”

It was then that it sort of made sense for Sam. It wasn’t that Dean felt the same way. Dean must have found out somehow about Sam’s feelings and been disgusted. That had to be why. Or maybe Dean was just tired of him. He couldn’t tell which was worse.

“I’ll be better, De. I promise. I won’t get in the way. I’ll change.” Sam sobbed pathetically. Dean just shook his head and pulled away. Sam got up from the bed and gripped at his brother’s shirt.

It was almost comical how long they stood like that. Sam was breathing heavily like he’d just ran a marathon and Dean’s fists were shaking, his back to his little brother. Sam eventually let out a long sigh, a sign of defeat.

He loosened his grip on Dean’s shirt and just wrapped his arms around the older boy’s waist and let his head rest against the middle of Dean’s back.

“Just don’t forget about me.” Sam mumbled into Dean’s shirt. The older brother sighed and let his warm hands rest against Sam’s skinny arms.

“That’s impossible, Sammy.” Dean mumbled, then added, “I’ll call you every night.” He promised. Sam took that for what was and finally let go. Dean could hardly spare Sam a glance before he was out the door.

Suddenly, Sam wasn’t so hungry anymore. His legs felt weak as he made his way to his bag and shakily pulled out Dean’s sweater.

The smell of him was nearly gone, but it was enough. It wasn’t like Dean had left yet, but Sam knew it’d be soon, probably that same night. So he put the too big sweater over his lanky form and curled into a ball on his bed.

He didn’t know how long it was going to hurt. So he just wrapped his arms around himself and pretended it was Dean. That Dean wasn’t planning on leaving him.

And when night finally rolled around and Dean was putting his bags in the back of the Impala, Sam faked a smile. He still had the sweater, not caring about the looks Dad or Bobby gave about the fact that it stopped just over his knees. Sam only cared about the slight blush it gave Dean, no matter how confused it left him.

John gave Sam an awkward hug, and in his own reserved way, told Sam that he loved him. Dean’s embrace was short and only ended with him ruffling up Sam’s hair and saying, “Be safe, Sammy.”

Sam supposed their real goodbye happened that morning. He supposed he was okay with that.

Bobby placed a comforting hand on Sam’s shoulder as the Impala drove away from the salvage yard. _Merry fuckin’ Christmas_ , Sam thought bitterly as they disappeared from sight.


	2. Chapter Two

**Notes for the Chapter:**

> Tags updated! Please take a look at them just in case

_**Summer, 1996** _

Sam wanted to blame summer for the way he changed. Or maybe he even wanted to blame it on Dean leaving. It took a few weeks for him to realize that the blame didn’t fall on one specific person. It was just who he was and what he always liked, even if he couldn’t admit it to himself before. And maybe he shouldn’t even be thinking about it that hard. All he knew was that he looked beautiful. And all of his friends told him so as well.

He wondered if Dean would think so too as he looked into his friend’s full body mirror. He had her plaid skirt on and it fit snuggly around his waist and stopped mid thigh. The tank top was his own from when he was smaller and it was tight, showing the curve of his waist.

His friends stood behind him, their eyes wide. “Sam.” Raven gasped. Charlie was on the other side of him, her eyes wide. “You are so pretty.” The red head said with a smile.

Sam couldn’t help the smile that graced his features. They had done his make up too, a light coat of gloss and mascara that somehow made his eyes look brighter.

He couldn’t help but wonder what Dean would think. Would he think that Sam looked pretty? The thought made him blush and wrap his arms around himself. His friends didn’t seem to notice as they took turns brushing out his hair.

“Are you sure you’re not like me? Because holy shit, Sam.” Raven asked as she looked the young Winchester over. Sam gave her a soft smile and nodded his head. He didn’t want to be a girl or anything. He just liked dressing like this sometimes. It was exciting.

Raven nodded like she understood where he was coming from and started giving him more items to try on. Fish net stockings, combat boots, and a choker to finish off the look. Sam was grateful that they wore the same size clothing.

All the while Charlie was in the background getting their party stuff together. They had the night to themselves seeing as their parents were out of town.

Charlie came back into Raven’s room with alcohol and pulled Raven’s private stash of weed paraphernalia from her closet. Raven didn’t seem to mind as she fell against her plush duvet to help her step sister roll the joints.

Sam was still looking at himself in the mirror. He felt like a different person. His heart raced as his hands roamed his flat chest and over his slim tummy. He knew it was stupid, but he couldn’t help but imagine Dean’s hands on him, telling him how pretty he looked. Kissing his forehead and calling him his.

“Hey, you good, Sam?” Charlie asked. He turned to the red head and gave a forced smile.

“I’m good.” Sam said as he finally tore himself away from the mirror. He sat at the end of the plush bed and didn’t refuse the joint as it was handed to him.

The night soon turned into a blur after that. He felt free as he drank, smoked, and danced with his friends. Sam lost his filter as he talked about the guy he was totally obsessed with. He thankfully had enough mind to leave out the name and the fact he was talking about his own brother.

“Does he have email?” Raven asked in a slurred tone. Sam nodded in response but it his mind was on the glowing stars plastered onto her ceiling. What caught his attention though was a bright flash of light coming from above him.

“Raven!” Charlie giggled. Sam blushed deeply as the after affects of the flash finally left his eyes. Raven was standing above him, camera in her hand, a devilish smile playing at her lips.

“Let’s show that boy what he’s missing.” The dark haired girl declared. Sam gulped and gave a slow nod.

“T-try not to get my face in it okay?” Sam asked through a stutter. He knew it was a bad idea, but he couldn’t find it in him to care. Sam had a feeling he wouldn’t remember much anyway as he took more hits and a few more shots. His inhibitions faded more and more as Charlie helped him get in various positions, all while hiding his face.

He didn’t even remember the two step sisters downloading all of the images to their parent’s desktop. He just remembered Charlie saying something along the lines of, “we really gotta delete these before our parents get home.” He also remembered laughing so hard at the concept before vomiting on their bathroom floor.

Things calmed down after that. He slept peacefully in the middle of Raven’s soft bed, with the two girls on each side of him. The sight may have looked weird on the outside but Sam accepted at the end of that school year that he wasn’t attracted to girls at all. And so all he could really say was that he felt good in the arms of his two best friends.

He woke up with the worst migraine he ever had in his young life. Still though, he remembered nothing. He had gotten black out drunk, or was it black out cross faded? Sam wasn’t sure. Dean would be so proud, he thought sarcastically as he got up and washed his face. He had to at least look somewhat presentable for his long walk back home.

~*~

Days pass and Sam hadn’t gotten his usual nightly call from Dean. It was making him anxious. He’d stay up late at night wrapped up in his brother’s sweater and hoped that he’d hear the house phone ring, but all that ever came out of it was silence.

Bobby assured him that Dean and his father were both fine, just busy on a hunt. It still didn’t ease Sam’s nerves. Bobby didn’t let him go out again that weekend after he came home smelling of weed and alcohol, so all the boy could do was stew in his own anxiety when he wasn’t helping Bobby with the junkers outside.

It was a Sunday evening when the phone rang throughout the house. “Get that, Sam. I gotta head to the store.” Which probably meant he had to go see sheriff Judy Mills and somehow thought Sam was clueless enough to not the find out.

Not that Sam really cared at that moment. Because as soon as the front door shut, he ran to the phone in the kitchen and picked it up off the receiver.

“Hello?” Sam called out, his tone more hopeful than he’d meant to let on. There was a breathy laugh from the other end and Sam could feel his chest fill with warmth.

“Missed me, Sammy?” Dean asked jokingly. Sam scoffed unconvincingly, and it made the older Winchester hum. Sam sat at the table and awkwardly trailed his fingers over the phone’s cord.

“How’s the hunt?” Sam asked, desperate to make conversation.

“It’s a slow one. Still picking up leads. We reckon it’s a vamp nest nearby.” He paused as Sam asked where John was, then said, “He’s out getting supplies. Said I’ve been a little too irritable for his taste.”

Sam could hear the sound of Dean taking a sip of beer. He was drinking. “Are you... drunk?” Sam inquired in a whisper for whatever reason. It made Dean chuckle.

“You are just _filled_ with questions tonight, huh, Sammy?” Dean teased. “In that case, I have a few questions of my own. First off, who was that girl in those pictures you emailed me?” Dean asked, wasting no time to get straight to the point.

Sam was silent for a moment as he tried to think back to what Dean could he referring to.

“She was real pretty,”. Dean supplied, “long legs, tiny skirt.” He whispered, the sound of it sending shivers down Sam’s spine. Sam licked his dry lips, his mind still drawing a blank.

“Couldn’t see her full face but she had shiny red lips. Looked sweet enough to kiss.”

It was that one simple sentence that caused Sam to let out a sharp breath. Memories flooded back into his head of nights ago when he was drunk and high with his friends and being so incredibly stupid.

“O-oh... I... Dean, that was an accident.” Sam tried, his voice quivering. He couldn’t believe he did something so idiotic.

“Was it though, Sammy? I think you wanted big brother to see.” Dean said, his tone deep and husky. It made Sam’s face flush with heat. Dean was drunk and not making any sense.

Sam let out a shaky breath. “That... no, I...” He was at a loss for words. Dean chuckled softly, the sound hot and borderline teasing against the boy’s ear.

“Don’t be so modest, Sammy. Should be proud of yourself for scoring like that.” There was something in the tone of Dean’s voice that Sam couldn’t place. The only thing he could think about were those pictures. Dean saw him like that and thought it was a pretty girl.

The situation, for whatever reason, made warmth fill the pit of Sam’s stomach. Though he may not have realized it, Dean was calling Sam pretty. And that excited the boy way more than it should have.

“What... what did you like best?” Sam asked carefully. Dean hummed in response, and Sam could feel his body tingle with anticipation.

“The legs are what caught my eye first.” Dean whispered, “long and slender. Bet they were soft under the fishnet, hm?”

Sam gasped softly, his hand falling to his lap. He knew this was wrong, that Dean really did have no idea what he was talking about. But Sam couldn’t help but eat up the praise.

“Y-yeah... felt good, De.” Sam whispered and he could almost swear he heard his brother curse under his breath. The sound made another shiver coarse through Sam’s body and down to his groin. This was dangerous, but Sam couldn’t find it in him to stop.

“S...she was so warm a-and tight, let me do whatever I wanted...” Sam stammered. That’s what he’d do for Dean. Anything. He’d let Dean use him anyway he wished.

“Yeah?” Dean whispered. There was rustling in the background and then Sam could hear Dean suck in a sharp breath. “Sounds hot, Sammy.”

Sam was reeling. He couldn’t believe he was doing this. Cautiously, he gripped at himself through his pants, biting his lip as to not make too much of sound as it relieved some of the pressure.

“De,” Sam said a little too innocently, and he didn’t miss the slight lapse in his brother’s breathing at the sound of it. His heart hammered in his chest as his hand slipped past his loose bottoms and wrapped around his length, “ _De_ ,” Sam let out once again in the form of a moan that completely shifted the air around them.

“Fuck, Sammy,” Dean ground out. There was a long exhale through his nose and Sam couldn’t help but imagine him in his ear, growling and claiming the teen as his own. Sam’s unsteady hand pumped up and down his stiff cock, his sounds getting less muffled by the second.

“God, baby boy... that’s it... Don’t stop.” Dean mumbled, his own breathing getting heavier. Sam whimpered softly at the sound of the pet name. He didn’t even care anymore that Dean was probably drunk out of his mind and just horny.

Sam needed this. He needed to feel like Dean wanted him. Even if this meant nothing to Dean. Even if Dean wouldn’t remember this happened. Nothing mattered more to Sam in that moment than the sound of Dean’s grunts in his ear.

“De, I, ah... need to...” Sam could barely get his words out. There was so much he wanted to say. He wanted so badly to have Dean right there with him. He wanted to be pinned down and fucked, wanted Dean’s come deep inside of him.

“Do it for me, baby. Let me hear you.” Dean ordered. Sam finally let go after that. He came hard, it coated his shirt and hand but he didn’t care. He never felt so good in his life.

Dean grunted loudly against the receiver and Sam just knew he was coming. He listened intently as Dean ground out the rest of his orgasm. Until there was nothing but silence on both ends.

“...Dean?” Sam asked after awhile. Seconds pass and he could hear the faint sound of his brother’s snoring. A sad smile graced his features as he tucked himself back into his pants and wiped his hand on his already soiled shirt.

“Goodnight, De. I love you.”

~*~

_**1997** _

The brothers never did talk about what happened over the phone. When Dean was sober, he acted like everything was fine. So Sam followed suit, seeing as he didn’t want to make things awkward.

All it really did though was make him feel lonely. He couldn’t make sense of it, no matter how hard he tried. And so, he didn’t. Sam would go out with his friends, go to school, and pretend everything was okay. During the day, anyway.

He’d still have those nightly conversations with Dean and pretend like he didn’t just want to cry about how much he loved him every time.

And after that, when he was alone with nothing but his thoughts, you’d still see him wrapped up in his brother’s sweater no matter the weather.

~*~

_**May 2nd, 1998** _

Dean was supposed to be there. He promised he would. It was Sam’s birthday and Dean was nowhere to be found. Sam had declined all the plans his friends tried to make for him simply because he only wanted to spend it with his big brother.

“Where are you at, Dean?” Sam asked, his tone harsher than he originally intended. He had been calling the hotel’s phone for hours, and when Dean finally answered, he was more than overwhelmed.

Dean sucked in a shaky breath. “I’m sorry, Sammy. I really am. We were on this hunt and it... it got bad.”

Sam was quiet for a few moments as he tried to process that sentence, the tone of Dean’s voice. He looked up to where Bobby was sitting with Jody on the couch, oblivious to the conversation Sam was having.

“What happened? Are you hurt?” Sam whispered. There was another shaky sound, almost like a sob, and it made Sam’s heart hammer in chest. Thoughts swirled in his head at every possibility, but still, nothing prepared him for what Dean said next.

“It’s dad. He... fuck,” Dean let out a real sob then and Sam could already feel the tears pooling in his eyes. “He got in between me and a werewolf. It’s not looking good, Sammy.”

Processing that was even harder. He didn’t realize he was crying until Bobby and Jody were in view, asking him what was wrong. Sam didn’t know what to say. Bobby just took the phone from him and talked to Dean all on his own, and all Sam could do was half listen to Jody as she tried to help him with his breathing.

Sam knew what it meant to get hurt by a werewolf. If his dad somehow survived the attack, he’d change. John wouldn’t want that. Either way, he was... Sam couldn’t let himself finish the thought.

John Winchester wasn’t perfect. He was far from it. But that was still Sam’s father. And in the end, he gave him what he always wanted: a normal life. Even if that life was without Dean. And that had been a choice his older brother made all on his own.

“Sam, are you okay to take the phone? Your dad wants to talk to you.” Bobby said carefully. Jody gave Sam one last look over and tried her best to wipe his tears away. He tried to give her a small smile at least for the effort, but he could hardly manage a nod.

With a shaking hand, he took the phone from Bobby’s grasp. “Hello?” Sam said. Bobby and Jody left him alone so they could speak privately, and Sam felt as though the walls were going to close in on him.

“Hey, Sam.” John said, his usually deep tone strained. “I’m sorry this had to happen on your birthday. Dean and I... well, we were really looking forward to seeing you.”

Sam didn’t know how to respond to that. He remembered that he used to be quick to open his mouth. Not in that moment though as another sob wracked through his body.

“Don’t cry, son. You know how this goes. Things like this happen in this life and I knew that.” John said like somehow that was supposed to make it easier.

“Just... stop... fuck, just stop with that overly macho bullshit for two seconds to realize what you’re saying. You’re taking your own life just so you don’t have to be a werewolf? That—dad, you of all people would be the one who could control it-“

“Sam, stop. Breathe.”

Reluctantly, Sam did as he was told. He shut his mouth and took in a deep breath.

“That’s not the kinda life I want. I’ve made peace with that. This is already hard enough since... never mind.” John said the last part in a long sigh. Sam didn’t have it in him to argue.

“Okay, then.” Sam breathed, and just for the moment, he dropped his own guard to say, “I love you, dad. I know I didn’t tell you that much. Even if you were a shit parent, you were the only one I had and I know it was hard on you. For that, I love you, okay?”

Sam had never heard his dad cry before, but after that, he could have sworn he heard the older man let out a soft sob and then disguise it as a cough.

“I love you, too, Sam. I wish I... I wish I could have done better for both of y’all. I have a lot of regrets I’m takin’ with me to the grave. I don’t want you two to live like that.”

Sam scrubbed a hand over his face and let out a shaky breath. “I know,” was the only thing he could let out. They sat on the phone for a few moments in silence until he heard Dean in the background, muffled as to not let Sam hear, the young man would bet.

And then John had to go. Leaving Sam alone with nothing but the walls collapsing around him. He needed to get out before he lost his mind. And so, he dialed Raven’s number and he was just about to hang up before she finally picked up.

“Hey, birthday boy.” Raven said in her usual chirpy tone. He almost forgotten that she had caller ID. The reminder of his birthday felt like another stab to the heart.

“H-hey, Raven. Do y-you have any plans tonight?” Sam couldn’t hide the quiver in his voice. He could tell Raven noticed it as her voice changed to a more motherly tone. Her and Charlie were both good for that.

“I mean, I did, but I can cancel them if you need me to. It was just this party this rich kid Brady is throwing up town. You’re more important though.”

Sam couldn’t help but smile then. He really did appreciate his friends. “Actually... I think a party is exactly what I need right now.”

Just like he expected, Raven liked the sound of that. He tried his best to look presentable, but it was hard to do that when his face was all red and splotchy from crying.

When Raven finally did show up, Bobby was almost reluctant to let Sam leave. But then Jody said something along the lines of letting Sam have some space and the teen couldn’t be more grateful.

Raven had Charlie in the passenger seat and as soon as they saw him, they took him back to their place to help him out a bit. Some concealer to cover up the redness, mascara and eyeshadow to make his hazel eyes pop, and then the dress.

He needed, more than anything, to be different that night. So when he saw himself in Raven’s thigh high, skin tight, dress on his body, he immediately felt happy. They assured him that there would be no homophobic assholes there, not that Sam was too worried about it. He didn’t give a shit about what anyone else thought. Not that night anyway.

Sam didn’t want to feel anything. He wanted to be numb. So when he was handed a beer and later a bong, he didn’t refuse them. And when Brady saw him from across the room, eyes trailing up and down his body, Sam made the first move.

“Sam, right? I’ve seen you around school.” Brady said, his eyes on Sam’s ruby red lips. “Hope this isn’t too forward, but you look really pretty tonight.”

Sam gave him a coy smile and stepped closer, “you think so?” He asked as he fluttered his long lashes. He’d never done anything like that before. He thought he would be more scared. In that moment though, he couldn’t really feel much of anything.

“Yeah.” Brady whispered. He was a little older, a senior, so he stood just a bit taller than Sam. He had a feeling that in a few more years he’d tower over most people, but for the moment, he was okay with looking up at Brady. Even if later on when he followed him up the stairs and into his bedroom he just shut his eyes and pretended it was Dean.

Sam could at least pretend that it was his brother kissing him up against the door. He could pretend he had actually came down for his birthday and gave his Sammy exactly what he always wanted.

Sam could easily pretend it was Dean laying him down on all fours, prepping him with his fingers. “De...” Sam mumbled drunkenly in the pillow. Brady was none the wiser as he talked about how tight Sam was. He didn’t need to know that Sam was a virgin. It didn’t matter.

“Fuck,” Brady cursed as he pressed inside. Sam had at least peeked to make sure he was using a condom and more lube. Still didn’t make it hurt less. He wasn’t going to tell him to stop though.

Sam just shut his eyes and waited for the pain to fade away. Raven had explained before what anal sex was like, how good it felt after the initial stretch and burn. And she had been right.

Sam gripped at the sheets, eyes rolling back as he imagined that Dean was the one fucking into him, the one telling him how hot he looked and sounded. He could hardly remember changing positions, but somehow he was on top, riding him. He wasn’t facing him, it made it easier pretend.

“That’s a good boy.” He groaned, and it made Sam whimper. “You like that, huh?” Brady teased. Sam rolled his hips in response, the tip of his cock hitting in Sam’s prostate just right. It helped him slip back into the space he was just in, that it was Dean talking to him like that.

Brady gripped at his hips an thrusted into him, hard. Sam gripped at Brady’s shins for support, eyes rolling back at the repetitive assault on his prostate.

“De...an...” Sam moaned brokenly. Brady was too distracted to even realize the world Sam was in. A world where it was just Sam and Dean. No death, no monsters. Just brothers. Just lovers. Nothing else would matter, not even—

_Dad, I don’t know..._

Sam’s eyes opened wide. His brother’s voice echoed in his head and Brady was pushing him back on all fours, fucking into him at a too rough pace.

_I don’t think I can do this._

Sam gripped at the seats, air getting caught in his throat. Brady was oblivious to it all as he gave Sam a hard spank.

_No, I... okay. Okay. I’ll do it._

Sam let out a sharp gasp. Tears leaked onto the sheets, and just as another hard slap ripped across his ass, a gun shot echoed loudly through his skull.

His sobbing was what finally made Brady stop. And Sam was grateful for that. He was thankful for the space as he curled up into a ball into the middle of the bed, crying and shaking.

“Hey, are you... did I hurt you? Was I too rough?” Brady asked from the edge of his own bed. Sam just shook his head, unable to form words as they only turned into mangled cries. Mascara was running down his face and he just felt so stupid and broken.

“I’ll go get help.” Brady said somewhere in the distance. Sam just curled into himself, wishing he had Dean’s sweater to protect him. Or just have Dean there all together.

_De... Dean... can you hear me?_

Sam didn’t know why he was trying that. It was so stupid. He was sure there was a logical explanation for what happened, trauma and all that.

Charlie and Raven made their way into the room. Raven was picking up articles of clothing off the floor, keeping her movements calm and slow. Charlie gently set herself on the bed, giving Sam enough space to make him feel somewhat comfortable.

Soon enough Raven was on he other side of him. He couldn’t deny that their presence was somehow comforting. He forced himself to lay on his back, his eyes to Brady’s ceiling.

“Did Brady hurt you?” Charlie asked, her tone soft and careful. Raven was cautious with her movements as she neared closer. Sam shook his head.

“Completely embarrassed myself on that one, huh?” Sam said through a light scoff. He scrubbed a hand over his makeup stained face. He truly felt numb.

Raven gently laid her hand over his wrist. “What’s wrong, Sam? You’ve been off ever since you called.” She was trying her best to be careful with her words. Charlie nodded like she agreed with Raven’s sentiment.

Sam licked his lips and shut his eyes. He was so mentally drained. He had no tears left to cry. He just felt empty.

“My dad died today.” The words felt hollow. He couldn’t open his eyes to see their reaction. He couldn’t take it.

Instead of them freaking out like he feared, they offered to take them back to their place. And he accepted. Though there was one thing he needed to get before that though.

Without a single complaint from Raven or Charlie, they drove him up to Bobby’s house. Luckily, he and Jody were fast asleep. It gave Sam enough time to wash his face and then go up to his room to get Dean’s sweater.

He held it in his hands for a few moments before holding it close to his chest. He wished Dean was there. He wanted Dean to hold him. Sam wanted to hold Dean.

_Dean..._

_Can you hear me?_

_Was what I heard earlier real?_   
  
_If it was... Are you okay?_

Sam supposed he didn’t need an answer to know the truth. Dean pulled the trigger so John wouldn’t have to.

When Sam made it back to the car, he had Raven’s dress folded in his arms, and was wearing Dean’s sweater and a pair of jogging pants. He let his head fall against the window and tried to let the music coming from the radio calm him down. And maybe it would have if a familiar voice didn’t ring through his ears.

_I hear you, Sammy._

Sam clung to the bottom of the sweater and sucked in a sharp breath. Dean could hear him. And that, for whatever reason, gave him just enough comfort to get through the night.


	3. Chapter Three

**_1998_ **

The months after his birthday had been rough. He couldn’t help but feel guilty for feeling that way. Dean was the one that had to pull the trigger. Dean was always the one having to make the hard calls.

But Sam was slipping. His friends noticed, Bobby noticed. Even Dean could tell.

Dean’s voice was a gentle whisper in the back of Sam’s mind,

_Don’t worry about me, Sammy. You gotta worry about yourself right now. Talk to somebody._

Sam knew he was right. Truly dark thoughts had been swirling in his mind, thoughts he couldn’t dare say out loud. But Dean had heard them, those nasty little thoughts.

And so, that was how Sam found himself talking to his school counselor. He was careful with his words; couldn’t bring up hunting or even his feelings for Dean. He worked around it, and honestly, it felt nice having a professional to talk to.

_Just wish you had someone to talk to, De. You probably need it more than I do._

_I’m fine, Sammy._

Sam knew there wasn’t much to argue about. Dean didn’t like to talk about the past. Sam laid in bed and traced his fingers over Dean’s sweater, humming softly to himself.

_You still wear that?_

The question made Sam gasp and blush. _You can see me?_

_It was just a second. Like I was looking through your eyes._

His tone was unusually soft. It made Sam feel all warm inside, despite his slight embarrassment.

_It makes me feel safe. Like you’re here with me._

Dean was silent. And in those few moments, Sam couldn’t help but feel shameful. Was it bad that this sweater made him happy? He was just about to ask when Dean’s voice came back to him.

_That necklace you gave me? I still wear it to this day. Whenever I’m sad, or in a dark place, I look at it and think of you. It keeps me grounded._

For whatever reason, Sam could feel tears prickle at his eyes. It was just a flash, but Sam could see through Dean’s eyes, the ratty motel room he was staying in, and then the amulet around his neck.

“De,” Sam sobbed out loud. The sight warmed his heart. Though there was one thing he still couldn’t wrap his head around.

_Let me be here for you in person. I miss you so much it hurts. Don’t you feel that too?_

Sam hadn’t brought up the subject since his birthday. That was the last time he expressed the need for Dean being there in person. Before that and after, Sam didn’t have the guts to say anything.

_Of course I feel that. I think about you every day, Sammy._

_Then come home. Be with me, Dean._

Sam’s heart hammered in his chest and he didn’t understand why. It wasn’t like it was a full confession. He wanted Dean with him, even wanted to be his, but he’d take what he could get just to be in his brother’s presence.

It was silent for a long while before Dean responded. Sam expected it, but it didn’t make it hurt any less.

_Can’t. Not yet. I need space right now okay? I don’t... I don’t think I can be around you yet._

Sam didn’t know what that was supposed to mean.

_I feel like I failed you. I failed Bobby. The rest of dad’s friends. For right now, I need to be alone. That’s not your fault, okay? I need you to know that. It’s just what I need right now._

Sam let out a soft sob and wrapped his arms around himself, around the warm sweater.

_I understand. I love you, De._

Sam had half expected Dean to tell him to stop the chick-flick moment. He was surprised to find that wouldn’t be the case.

_I love you, too, Sammy. So much._

Dean didn’t go too far after that, murmuring sweet little things into his baby brother’s mind to help him fall asleep.

~*~

**_1999_ **

Time seemed to fly by as Sam got his license, an old car thanks to Bobby, and his first job. The job itself was nothing fancy, but he loved it. It was a newly established coffee shop meant to be a safe place for LGBTQ+ youth. Sam didn’t know how long it would last in this city, but he was grateful to have it for the time being.

Sam was able to be himself there. He could be as pretty as he wanted with no complaints from coworkers. Maybe some costumers here and there, but his manager shut them down pretty quickly. And it also helped that his favorite coworker was one of his best friends: Raven.

She was starting to grow into her own person, too. Raven finally found a doctor that was willing to start her on hormone therapy. She was happy and Sam couldn’t help but be happy for her.

Charlie got a paid internship with one of the big businesses in Sioux Falls. She was definitely going places. Sam was proud of her, too.

Sam didn’t exactly know what he wanted to be. He made straight A’s in school, was even in Honor’s Society with Charlie.

He could get into any college he applied to. Hell, he could even get a couple of scholarships. Even Bobby told him money wouldn’t be an issue.

Sam still had no idea what he wanted. He had time to figure it out, sure. Hopefully in that time he’d find something that called out to him.

Brady still hung around for some reason. Sam had thought that after their more than awkward hook up he’d want nothing to do with Sam, but seeing as he was on vacation, he actually wanted to see Sam. And the sixteen year old had nothing better to do, so he accepted.

_You goin’ on a date, Sammy?_

Sam gave his reflection a sad smile. His outfit was simple, just some ripped jeans with a skin tight, pink tee tucked into it. He had thought about wearing his brother’s sweater because it was chilly outside but somehow that felt odd. So he settled with a his jean jacket, not giving a damn about what people thought about denim on denim.

 _Yup._ Sam replied simply.

_Oh. Okay. You... you look really pretty._

Sam’s heart thudded in chest. Dean thought he looked pretty? His hair was long, stopping just above his shoulders. He had it parted down the middle, one side pinned back. And he was only wearing a light coat of concealer and mascara. It still made him feel good.

_Thank you, De... I’m nervous._

It was the truth. If Brady had said he wanted just a hook up, that’d be fine. Sam could handle that. But he said a date, and that was something the sixteen year old was not used to. He wasn’t sure if he could trust it.

_Don’t be. He should be the one that’s nervous. I would be._

Sam couldn’t help it, a soft smile graced his features.

_You would, huh?_

He could practically feel Dean roll his eyes at that.

_You know what I mean._

_No, I don’t think I do. I think you may have to elaborate a little more._ Sam couldn’t help it as he teased his brother.

 _You are such a brat._ Dean’s tone was soft, no heat to it whatsoever.

_You’re just... you’re just great, Sam. You bright up a room just by being there. You’re empathetic, and strong, and beautiful—_

Dean stopped himself abruptly and for some stupid reason, the words brought tears to Sam’s eyes. He blinked them away as to not ruin his make up.

_What I’m trying to say is, any guy would be lucky to have you._

Sam didn’t know what to say. All he could do was wish Dean meant it the way he wished he did.

It was ridiculous that Sam still felt that way about his brother after years of separation. He still loved him just as much as the day Dean gave him that sweater and this link that they shared didn’t help matters.

 _Anyway,_ Dean sighed, _Good luck on your date. If anything bad happens, shoot me a thought and I’ll get Bobby to make a scene._

Sam chuckled and shook his head.

_Will do, Dean. Will do._

~*~

The date itself wasn’t bad, but Sam still couldn’t bring himself to enjoy it as much as he should had. It was stupid, he knew that. He wished he could shut off the fact that he wished Dean was the one sitting in front of him.

Was that obsessive? Sam wasn’t sure anymore. He tried his best to fake a smile as Brady talked about college life. He laughed, a hollow sound that Brady found sweet. It didn’t take long before they were back in the older boy’s car.

Brady’s lips were on his after a few minutes of meaningless conversation and Sam didn’t know what else to do other than let it happen. He had a sinking feeling that was all Brady wanted anyway. And maybe Sam wanted it, too. It was hard to tell. Maybe he wanted to forget his feelings about Dean, for just one night.

Maybe Sam didn’t think that through. Maybe he didn’t realize that being back in the older boy’s room he’d remember exactly what it was like to hear that gunshot.

“Hey, it’s okay.” Brady whispered. “Do you want me to stop?” His voice was unnervingly gentle as his fingertips brushed through Sam’s locks.

Sam took in a deep breath. He felt like he had to do this, for some reason he couldn’t describe. Maybe it would help him move on from it all.

“We can keep going.” Sam said just before pressing his lips back against Brady’s. The older boy hummed in approval. It didn’t take long until they were both naked and Sam was on his back, looking up at him.

He had to keep his eyes on him, because if he didn’t, he’d think of Dean. He didn’t want it to be like last time. So he moaned Brady’s name instead as he fingered him open, even if it didn’t sit right with him at first.

“You sound so pretty, oh my god.” Brady breathed out as he scissored his fingers inside Sam. The younger boy threw his head back then and just let the feeling take over. His heart was pounding in his ears as those lubed fingers were soon replaced with a condom covered cock.

He sucked in a deep breath at the intrusion. He hadn’t been fucked since that night, so it was like his first time all over again.

“You okay?” Brady asked. Sam sucked in a deep breath as his eyes fluttered open. He gave a hesitant nod in return. Luckily, Brady’s moments were still slow, his eyes watching Sam’s every facial twitch.

Sam shut his eyes again. It was almost too intimate to look in his eyes. But maybe that was a mistake, because just as those hazel eyes closed, he was met with the image of a familiar hand wrapped around an unfamiliar cock.

It was barely a second, but one glance downward showed an amulet and Sam knew exactly what he was seeing. Sam let out a sharp gasp, the sound making Brady’s pace quicker.

Sam concentrated as hard as he could, he didn’t want the image to go away. He wanted to see Dean pleasure himself, even if it had nothing to do with him—

_God, Sammy,_

The younger Winchester couldn’t help it as his eyes shot open. The sound of Dean moaning his name rang through his mind and he could hardly believe it.

Could Dean see what was happening? Could he see Sam being fucked relentlessly into another man’s mattress? The thought was paired with a particularly hard thrust to his prostate.

“Oh God,” Sam gasped as his hands fell from Brady’s shoulders. He wrapped his hand around his own length. He wanted to give Dean a good show.

Sam couldn’t help it as he moaned Dean’s name over and over again in his own head. He could still see Dean touching himself, his pace faster than before.

_Fuck, Sammy, I..._

It seemed as though Dean was at a loss for words as he lost himself in the pleasure of it all.

_Wish he was you, De,_

That single confession caused a strangled sound to come from the older Winchester, the sound echoing through Sam’s mind as Dean came over his hand.

Sam did that. He made his big brother feel good. Seeing Sam like that made Dean so hot and bothered that he couldn’t control himself. And that was what finally made Sam come, the spurts of white covering his stomach and chest.

_Holy fuck, Sam,_

It took Sam a little bit to realize that Dean and Brady said that at the exact same time. After that, Dean was silent, and Sam was forced to concentrate on the man above him.

“You’re so hot, and tight, I’m so fucking close.” Brady groaned as he gripped at the back of Sam’s knees . His thrusts were hard and erratic and Sam’s body was so overstimulated that it almost hurt. He wanted it to be over with, so Sam talked him through it, his tone soft and sultry.

“You feel so good,” Sam breathed out convincingly, “I know you wanna come, so do it, Brady. Come for me.” He said the last part in a mere whisper, and it made Brady practically growl. He crashed his lips onto Sam’s as he came, and Sam let him. He kissed back as much as he could but didn’t complain as the older boy finally pulled away.

Sam was silent as Brady pulled out and threw away the condom. He didn’t know what to expect as Brady laid back down beside him, but surely didn’t foresee the boy wrapping his arms around his slender form. Sam tensed up, not knowing exactly what to do.

_Dean?_

Sam was met with nothing but radio silence. All the good feelings he just had slowly slipped from his being. All he had was Brady’s embrace, and though he wished it was Dean’s, his brother was nowhere to be found. So Sam let himself lay against the older boy’s chest. He let himself bask in the comfort of it just a little while longer.

~*~

It’d been days with no word from Dean, not even a call. Sam could feel the panic set in. It was like his own thoughts had a stutter as he tried to talk to Dean, all of which were met with nothing but silence.

Sam found himself slipping back into that dark place. He stopped seeing the counselor, continuously showed up to work late. Raven and Charlie were worried, but Sam couldn’t bring himself to talk to them about anything.

Until one day when Bobby called him out on it.

“I can’t sit back and watch this anymore, Sam. You need to get your act together. Your grades are slipping and the only reason you haven’t been fired yet is because your boss is legitimately worried about you. We all are.” Bobby’s tone softened near the end, and it was only that that made Sam not go off instantly.

The boy let out a long sigh. “I don’t know what’s wrong with me, Bobby.” He supposed that wasn’t the whole truth. He didn’t know how to explain the psychic bond he shared with Dean and how he felt empty inside when he didn’t hear Dean’s voice inside his head.

“I can’t help you if you don’t open up to me.” Bobby said, his tone sincere. Sam scrubbed a hand over his face and let himself think that over.

He wanted to be okay. He wanted to keep his job and his friends. He didn’t want them to disappear. But he couldn’t tell Bobby about his real problem. Sam couldn’t tell anyone. It was wrong and he was already embarrassed enough.

So he went with what was closest to the truth, and somehow, even that made him feel a little bit better.

“I miss dad and I miss... I miss Dean.” He said his brother’s name in a mere whisper. Sam didn’t miss the look of sympathy on Bobby’s face as he listened to what the young man had to say.

“I have noticed that he hasn’t called as much as he used to. You know that can’t have anything to with you, right? He has a lot going on, stuff that only he can sort out.”

Bobby was trying his best, but Sam unfortunately knew better. It was his fault. And after awhile, Bobby could tell he wasn’t really getting anywhere with Sam as he let out a long sigh of defeat.

“Just... call your friends. Get out of the house tonight and do something. I hate seeing you cooped up in here and sulking all day.”

Sam let out a defeated sigh after that. He knew Bobby was right. It wasn’t long after that when Sam picked up the phone to call his friends. They were happy to hear from him and that, paired with the fact they weren’t mad at Sam for spacing out so much, made the boy feel just a bit better.

They were just about to head out somewhere and were practically begging for Sam to join them. After assuring him it wouldn’t be another party with rowdy teens, Sam agreed.

The drive felt long. Even longer without Dean’s voice in his head. He opted not to think about that though, instead choosing to sing along with his two best friends.

When they reached their destination, it looked like an obvious bar. He gave them both an annoyed glare and they just laughed.

“Not that kind of place.” Was the only explanation Raven gave as they made their way to the entrance. No one was there to card them, so Sam was sure no alcohol would be served. When they stepped inside though, he could honestly say that it was just about the gayest place Sam had ever seen.

And that, for whatever reason, hyped Sam up more than it probably should have. The building was filled with so many diverse people.

What really caught his eye though, were the people on make shift stage.

People of all different body types were strutting up and down the runway in so many bright colors. Their dresses were mostly huge, sometimes small, and their makeup was nothing like Sam had ever seen.

“We had a feeling you’d like this place.” Charlie giggled as she nudged the young man with her elbow. Sam gave his friends a bright smile and followed them to a table to the far side of the room, were a person was sitting with a sign up sheet.

“Room for one more?” Raven asked as she motioned over to Sam. He looked at them with wide eyes. His friends weren’t joining him. The guy sitting down gave him an amused smile as he picked up his pen.

“You’re in luck. The last queen dropped out last minute. What’s your name?” He asked and Sam took in a deep breath before he could really answer. Was he in the mood for this? He couldn’t shake the thought that he needed to do it. And so, he did.

“Sam Winchester.”

The guy chuckled as he wrote it down on the last line, “That’s good enough for now. See ya on stage, Sam.”

Things moved rather quickly after that. He was pulled away from his friends who waved and blew kisses as he was practically shoved into a make up artist’s chair.

She seemed nice enough as she asked if he’d rather do his make up alone, like most of the other drag queens do. But he just shook his head. He only knew how to do the basic stuff. She nodded then, and moved swiftly to get the materials she needed.

Sam sat back and relaxed as his makeup was done and only flinched slightly when another pair of hands moved to his hair. They pulled his long hair into a low bun and placed some sort of cap over his head before replacing it with a huge wig.

“You’re perfect, darling.” The hair stylist said. Sam looked himself over, and he couldn’t stop the smile that took over his features. He wondered what Dean would say if he was there right then.

That one thought caused his smile to falter. Dean wasn’t there. Not even his head to tell him how pretty he looked as he’d done before. Not even there to tell him that he looked silly like the petulant brother he could be.

Sam shook his head. He couldn’t let those thoughts bring him down again. He didn’t know exactly what was going on with Dean-though he had an idea-all he really knew for sure was that no matter how much he still loved the man, Sam couldn’t let it drag him down anymore.

And though that was easier said than done, he knew there was no other way it could be. He knew well enough that his feelings wouldn’t just disappear. He loved Dean. He probably always would.

That didn’t mean he had to stop doing the things that made him happy. Or just not try new things all together like he’d done before.

A group of laughing people came bustling in, ripping Sam from his thoughts. Their eyes fell to his bashful face, a look of understanding fell upon them as the tallest one stepped up to Sam.

He reached out to Sam and helped him up and looked him over. “Looks like the stylist did a great job. You just about ready?” He asked, his smile kind. Sam nodded slowly, scared that his blush was showing through the make up.

They each gave him advice on what to do for his first performance. What Sam got out it of it was this: follow their lead. And so, he did.

He got on that stage and moved as they did. He smiled and laughed and for the first time in years, he felt truly light.

Charlie and Raven were right there at the front, cheering him on.

By the end of the night, he knew for sure that this was what he’d been missing. A good outlet outside of work and school. They even told him that they all hoped to see him next weekend. He’d make sure to make time for it.

He went back to the girls’ house after. They had one of their famous sleep overs. It felt like forever since they had one of those.

They each took turns taking a shower and Sam took the longest thanks to all the makeup. And when he was done, he took a long look at himself in the mirror.

His eyes were so bright. Not red from tears like they usually were. His hand unconsciously reached for something that wasn’t there, and his smile suddenly faltered.

Every night like clockwork, he put on Dean’s sweater. Slept in it or held it close. His heart felt heavy. It was so silly. It was just polyester, after all.

But Sam couldn’t help it. It was the only thing he had of Dean’s besides photographs Bobby had around the house. It was different for the simple fact that Dean had given it to him.

The need to talk to Dean was back at full force. He scrubbed a hand over his face and took in a long breath.

Sam was going to give it one more try, and that was it. He’d just put on his tee shirt and jeans and make his way back to his friends like nothing was bothering him if all he got was nothing.

He kept his eyes low as he called out to him, _you there, De?_

Sam gave it a few moments, and just as he expected, he was met with silence. He blinked away tears as he forced himself to get dressed and made his way to the door.

And just as his hand wrapped around the knob, the voice he longed for most finally filled his head.

 _I’m here, Sammy._ His tone just as soft as polyester.

**Author's Note:**

> if it wasn’t already obvious, this story is loosely based of Conan Gray’s song called Heather.


End file.
